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Details

Stereochemistry RACEMIC
Molecular Formula C11H17NO
Molecular Weight 179.2592
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-METHOXYMETHAMPHETAMINE

SMILES

CC(Cc1ccc(cc1)OC)NC

InChI

InChIKey=UGFMBZYKVQSQFX-UHFFFAOYSA-N
InChI=1S/C11H17NO/c1-9(12-2)8-10-4-6-11(13-3)7-5-10/h4-7,9,12H,8H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C11H17NO
Molecular Weight 179.2592
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment:: The description was created based on several sources, including http://www.who.int/medicines/access/controlled-substances/5.6_PMMA_CRev.pdf | https://www.ncbi.nlm.nih.gov/pubmed/28506818

4-Methoxymethamphetamine (PMMA, para-Methoxymethamphetamine) is a stimulant and psychedelic drug closely related to the amphetamine-class serotonergic drug para-methoxyamphetamine (PMA). Little is known about the pharmacological properties, metabolism, and toxicity of 4-Methoxymethamphetamine. Because of its structural similarity to para-methoxyamphetamine, which has known toxicity in humans, it is thought to have considerable potential to cause harmful side effects or death in overdose. In the early 2010s, a number of deaths in users of the drug MDMA were linked to misrepresented tablets and capsules of 4-Methoxymethamphetamine. In 2010–2013, a cluster of 29 fatal poisonings related to the toxic designer drug 4-Methoxymethamphetamine was revealed in Norway. The toxicity of PMMA is regarded as substantially higher than for amphetamine, methamphetamine, and MDMA, as indicated by 131 fatal and 31 nonfatal poisonings associated with the abuse of 4-Methoxymethamphetamine worldwide. The toxicity of 4-Methoxymethamphetamine is positively correlated with the 4-Methoxymethamphetamine dose and the blood drug level, but the existing literature indicates that certain human subjects may have an increased risk of 4-Methoxymethamphetamine toxicity. 4-Methoxymethamphetamine, like PMA most likely acts as a selective serotonin releasing agent (SSRA) with weak effects on dopamine and norepinephrine transporters. However, relative to MDMA, it is considerably less effective as a serotonin releaser with properties more akin to a reuptake inhibitor in comparison. It evokes robust hyperthermia while producing only modest hyperactivity and serotonergic neurotoxicity, substantially lower than that caused by MDMA.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
83.0 µM [IC50]
7.4 µM [IC50]
180.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Evaluation of the neurotoxicity of N-methyl-1-(4-methoxyphenyl)-2-aminopropane (para-methoxymethamphetamine, PMMA).
1992 Sep 4
Determination of a newly encountered designer drug "p-methoxyethylamphetamine" and its metabolites in human urine and blood.
2008 May 2
Patents

Sample Use Guides

doses typically >100 mg
Route of Administration: Oral
Human embryonic kidney (HEK) 293 cells stably expressing human DAT, NET or SERT were used for activity evaluation. Uptake activity of hNET, hDAT and hSERT was measured using the Neurotransmitter Transporter Uptake Assay Kit from MDS Analytical Technologies (Sunnyvale, CA). On day 0, HEK 293 cells were seeded at a density of approximately 60.000 cells/well in clear-bottom, black-walled, 96-well plates (Greiner Bio-one, Solingen Germany) coated with PLL buffer (50 mg/L). Cells were allowed to proliferate overnight in a humidified 5% CO2/95% air atmosphere at 37 °C. Experiments were performed the next day (day 1). Cells were pre-incubated with the fluorescent substrate for 12 min prior to a 30 min drug exposure. Culture medium was replaced by 100 μL/well fluorescent substrate solution, and uptake measurements were started. At t= 0, 100 μL/well HBSS without (control) or with drug was added to each well and uptake was measured continuously for 30 min. Background wells were pre-incubated with 100 μL/well HBSS without fluorescent substrate solution and exposed at t =0 min to 100 μL/well HBSS without drugs. Non-transfected HEK 293 cells pre-incubated with 100 μL/well fluorescent substrate solution and exposed at t= 0 to 100 μL/well HBSS without drugs served as negative controls. Drugs were prepared daily in HBSS from 2 or 100 mM stock solutions. Cocaine, DL-amphetamine, MDMA, 4-FA, MXE, PMMA, 2C-B, 25B-NBOMe, 25I-NBOMe, α-PVP and 5-APB were measured at final concentrations of 0.01–1000 μM.
Substance Class Chemical
Created
by admin
on Sat Jun 26 02:31:10 UTC 2021
Edited
by admin
on Sat Jun 26 02:31:10 UTC 2021
Record UNII
037U5SR9KL
Record Status Validated (UNII)
Record Version
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Name Type Language
4-METHOXYMETHAMPHETAMINE
Common Name English
P-METHOXYMETHAMPHETAMINE
Common Name English
BENZENEETHANAMINE, 4-METHOXY-N,.ALPHA.-DIMETHYL-
Systematic Name English
P-METHOXY-N,ALPHA-DIMETHYLPHENETHYLAMINE
Systematic Name English
PARA-METHOXY-N-METHYLAMPHETAMINE
Systematic Name English
4-METHOXY-N-METHYLAMPHETAMINE
Systematic Name English
J50.049F
Code English
PARA-METHOXYMETHAMPHETAMINE
Common Name English
RED MITSUBISHI
Common Name English
PMMA-
Common Name English
PARAMETHOXYMETHAMPHETAMINE
Common Name English
PMMA (AMPHETAMINE)
Common Name English
4-MMA
Common Name English
J529.268I
Code English
(+/-)-N-METHYL-P-METHOXYAMPHETAMINE
Common Name English
4-METHOXY-N,.ALPHA.-DIMETHYLBENZENEETHANAMINE
Systematic Name English
Code System Code Type Description
CAS
88543-18-4
Created by admin on Sat Jun 26 02:31:10 UTC 2021 , Edited by admin on Sat Jun 26 02:31:10 UTC 2021
SUPERSEDED
FDA UNII
037U5SR9KL
Created by admin on Sat Jun 26 02:31:10 UTC 2021 , Edited by admin on Sat Jun 26 02:31:10 UTC 2021
PRIMARY
WIKIPEDIA
PARA-METHOXY-N-METHYLAMPHETAMINE
Created by admin on Sat Jun 26 02:31:10 UTC 2021 , Edited by admin on Sat Jun 26 02:31:10 UTC 2021
PRIMARY para-Methoxy-N-methylamphetamine (also known as PMMA, Red Mitsubishi), chemically known as methyl-MA, 4-methoxy-N-methylamphetamine, or 4-MMA) is a stimulant and psychedelic drug closely related to the amphetamine-class serotonergic drug para-methoxyamphetamine (PMA). PMMA is the 4-methoxy analog of methamphetamine. Little is known about the pharmacological properties, metabolism, and toxicity of PMMA; because of its structural similarity to PMA, which has known toxicity in humans, it is thought to have considerable potential to cause harmful side effects or death in overdose. In the early 2010s, a number of deaths in users of the drug MDMA were linked to misrepresented tablets and capsules of PMMA.
ECHA (EC/EINECS)
244-917-6
Created by admin on Sat Jun 26 02:31:10 UTC 2021 , Edited by admin on Sat Jun 26 02:31:10 UTC 2021
PRIMARY
CAS
22331-70-0
Created by admin on Sat Jun 26 02:31:10 UTC 2021 , Edited by admin on Sat Jun 26 02:31:10 UTC 2021
PRIMARY
PUBCHEM
90766
Created by admin on Sat Jun 26 02:31:10 UTC 2021 , Edited by admin on Sat Jun 26 02:31:10 UTC 2021
PRIMARY
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